6,7-Didehydro- or 7,8-didehydro-PGI1 acyl-substituted phenyl esters

ABSTRACT

The present invention relates to novel acyl-substituted esters of 6,7-didehydro- or 7,8-didehydro-PGI 1  compounds, e.g., the 4-acetylphenyl ester of such PGI 1  analogs. These esters are characterized by pharmacological activity, being for example useful for the pharmacological purposes for which the corresponding free acids are employed.

The present application is a divisional application of Ser. No. 933,329, filed Aug. 14, 1978, now issued as U.S. Pat. No. 4,180,657, on Dec. 25, 1979.

The present invention relates to prostaglandin analogs for which the essential material constituting a disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,180,657, issued Dec. 25, 1979. 

I claim:
 1. An acid ester of a prostacyclin analog of the formula ##STR1## wherein L₂ is (1) --(CH₂)_(n) - wherein n is one to 5 inclusive, or(2) --(CH₂)_(p) -CF₂ - wherein p is 2, 3, or 4, wherein Q is ##STR2## wherein R₄ is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R₁ is alkyl of one to 4 carbon atoms, inclusive, with the proviso that when R₁ is tert-butyl the ##STR3## group is in the 4-position, wherein R₈ is ##STR4## wherein R₉ is ##STR5## wherein C_(g) H_(2g) is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR₅ R₆ -- and terminal methyl, wherein R₅ and R₆ are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R₅ and R₆ is fluoro only when the other is hydrogen or fluoro and the further proviso that neither R₅ nor R₆ is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C_(j) H_(2j) where C_(j) H_(2j) is a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR₅ R₆ - and the phenyl ring; wherein T is alkyl of one to 4 carbon atoms; inclusive, fluoro, chloro, trifluoromethyl, or --OR₇ - wherein R₇ is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2 or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different, andwherein X is (1) trans--CH═CH-- (2) cis--CH═CH-- (3) --C.tbd.C--or (4) --CH₂ CH₂ --.
 2. Δ⁶ -PGI₁, 4-Acetylphenyl ester, a compound according to claim
 1. 3. An acid of a prostacyclin analog of the formula ##STR6## wherein L₃ is --(CH₂)_(n) - wherein n is one to 5 andwherein Q is ##STR7## wherein R₄ is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R₁ is alkyl of one to 4 carbon atoms, inclusive, with the proviso that when R₁ is tert-butyl the ##STR8## group is in the 4-position, wherein R₉ is ##STR9## wherein C_(g) H_(2g) is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR₅ R₆ -and terminal methyl, wherein R₅ and R₆ are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R₅ and R₆ is fluoro only when the other is hydrogen or fluoro and the further proviso that neither R₅ nor R₆ is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C_(j) H_(2j) wherein C_(j) H_(2j) is a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR₅ R₆ -- and the phenyl ring; wherein T is alkyl of one to 4 carbon atoms; inclusive, fluoro, chloro, trifluoromethyl, or --OR₇ -- wherein R₇ is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2 or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different,wherein R₁₁ is hydrogen, hydroxy, or hydroxymethyl, and wherein X is (1) trans--CH═CH-- (2) cis--CH═CH-- (3) --C.tbd.C-- or (4) --CH₂ CH₂ --
 4. (6R and 6S)-Δ⁷ -PGI₁, 4-Acetylphenyl ester, compounds according to claim
 2. 